ethyl N-(4H-1,2,4-triazol-3-yl)acetimidate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl N-(4H-1,2,4-triazol-3-yl)acetimidate
• 英文别名: ethyl N-(4h-1,2,4-triazol-3-yl)acetimidate；ethyl N-(1H-1,2,4-triazol-5-yl)ethanimidate
• 化学式: C₆H₁₀N₄O
• 分子量: 154.172
• InChiKey: LQVDRWQSPKBHER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-(4H-1,2,4-triazol-3-yl)acetimidate 、 sodium thiocyanide 以 乙醇 、 水 为溶剂， 反应 12.0h， 以48%的产率得到7-methyl-5H-[1,2,4]triazolo[4,3-c][1,3,5]thiadiazin-5-imine
  参考文献：
  名称：

  Convenient Synthesis of [1,2,4]Triazolo[4,3-a][1,3,5]triazin-5-amines, [1,2,4]Triazolo[4,3-c][1,3,5]thiadiazine-5-thiones, and [1,2,4]Triazolo[4,3-c][1,3,5]thiadiazin-5-imines from N-(4H-1,2,4-Triazol-3-yl) Carboximidates

  摘要：

  The condensation of 4H-1,2,4-triazol-3-amine with ortho esters derived from acetic, propionic, and benzoic acids gave the corresponding N-(4H-1,2,4-triazol-3-yl) carboximidates which were treated with cyanamide, carbon disulfide, and sodium thiocyanate to afford 7-substituted [1,2,4]triazolo[4,3-a][1,3,5]triazin-5-amines, [1,2,4]triazolo[4,3-c][1,3,5]thiadiazine-5-thiones, and [1,2,4]triazolo[4,3-c][1,3,5]thiadiazin-5-imines, respectively. The structures of the synthesized compounds were confirmed by IR, H-1 and C-13 NMR, and mass spectra and elemental analyses.

  DOI：

  10.1134/s107042801910018x
• 作为产物：
  描述：

  原乙酸三乙酯 、 3-氨基-1,2,4-三氮唑 在 溶剂黄146 作用下， 反应 3.0h， 以65%的产率得到ethyl N-(4H-1,2,4-triazol-3-yl)acetimidate
  参考文献：
  名称：

  新的 1,2,4-Triazolo-1,3,5-triazin-4-ones 衍生物的新合成路线

  摘要：

  氯甲酸乙酯与衍生自 3-氨基三唑的亚氨基酯反应，然后胺或苯肼缩合，在 60-85 中生成多种 1,2,4-triazolo-1,3,5-triazin-4-ones % 总产率。

  DOI：

  10.1080/10426500500269380

文献信息

• Simple and efficient approach to synthesis of [1,2,4]triazolo[4,3-<i>b</i>][1,2,4,6]thiatriazine- 1-oxides from <i>N</i>-triazol-3-ylamidines
  作者：Azhar Hajri、Mohamed Lamjed Marzouki

  DOI：10.1515/hc-2017-0003

  日期：2017.4.1

  Abstract A facile method for the synthesis of [1,2,4]triazolo[4,3-b][1,2,4,6]thiatriazine 1-oxides 3a–h is presented. The approach involves a reaction between N-triazol-3-ylamidines 2a–h and thionyl chloride in the presence of pyridine. The structures of the synthesized compounds were confirmed by spectral studies including IR, 1H NMR, 13C NMR, MS and elemental analysis.

  摘要 提出了一种合成 [1,2,4] 三唑并 [4,3-b][1,2,4,6] 噻三嗪 1-氧化物 3a-h 的简便方法。该方法涉及在吡啶存在下 N-三唑-3-基脒2a-h 与亚硫酰氯之间的反应。合成化合物的结构通过光谱研究证实，包括 IR、1H NMR、13C NMR、MS 和元素分析。
• Novel 6-aryl-7-alkyl/aryl-[1,2,4]triazolo[4,3-a][1,3,5]triazine-5(6H)-thiones, processes for their preparation, characterization and evaluation of their in vitro antioxidant activity
  作者：A. Hajri、D. Alimi、K. Rtibi、H. Sebai

  DOI：10.4314/bcse.v35i3.8

  日期：——

  ABSTRACT. A series of nine new 6-aryl-7-alkyl/aryl-[1,2,4]triazolo[4,3-a][1,3,5]triazine-5(6H)-thiones (2a-i) were synthesized by a reaction of N-triazol-3-yl imidates (1) with three different isothiocyanate derivatives (RNCS)  in refluxing toluene. The structures of the final heterocyclic compounds were confirmed by 1H-NMR, 13C-NMR, FT-IR, elemental analysis, and mass spectral analysis. The target compounds (2a-i) were in vitro screened for their activity as antioxidants using DPPH (2,2′-diphenyl-1-picrylhydrazyl) and FRAP (ferric reducing/antioxidant power) methods. The results revealed that some triazolotriazine-5-(6H)thiones exhibited antioxidant activity ranging from moderate to high. The obtained findings revealed that the triazolotriazine-5-(6H)thiones (2g, 2h, and 2i) have superiority among all compounds, It is obvious that the presence of a hydroxyl group in the structure is essential for the antioxidant properties and should be taken into consideration in further design of structures with potential antioxidant properties.                     KEY WORDS: Imidates, Isothiocyanates, Antioxidant, Triazole, DPPH, FRAP   Bull. Chem. Soc. Ethiop. 2021, 35(3), 565-572. DOI: https://dx.doi.org/10.4314/bcse.v35i3.8

  摘要：通过N-三唑基咪唑酯（1）与三种不同的异硫氰酸酯衍生物（RNCS）在回流甲苯中反应，合成了九种新的6-芳基-7-烷基/芳基-[1,2,4]三唑并[4,3-a][1,3,5]三嗪-5（6H）-硫酮（2a-i）。通过1H-NMR、13C-NMR、FT-IR、元素分析和质谱分析确认了最终杂环化合物的结构。使用DPPH（2,2'-二苯基-1-苯肼）和FRAP（铁还原/抗氧化能力）方法对目标化合物（2a-i）进行了体外抗氧化活性筛选。结果表明，一些三唑并三嗪-5-(6H)硫酮表现出从中等到高的抗氧化活性。获得的发现表明，三唑并三嗪-5-(6H)硫酮（2g、2h和2i）在所有化合物中具有优越性。显然，结构中羟基的存在对抗氧化性质至关重要，并应在进一步设计具有潜在抗氧化性质的结构时予以考虑。 关键词：咪唑酯，异硫氰酸酯，抗氧化剂，三唑，DPPH，FRAP 《埃塞俄比亚化学学会志》2021年第35卷第3期，565-572页。DOI：https://dx.doi.org/10.4314/bcse.v35i3.8